For a significant number of stars, appearing in Playboy is a sign of failure: When you can't get hired as a singer, actor or TV presenter, the magazine still has a job for you. Lindsay Lohan's January Playboy pictorial is an obvious example, but you'll be surprised at the number of huge stars whose airbrushed images essentially wrote "The End" on their careers.

Kathleen Turner, Paris Hilton and Mariah Carey have all experienced the Curse of Hef. (It happened to Shannen Dohertytwice!)